The present invention relates to 1-(aryloxy)propionoyl-2-arylsulfonyl hydrazines useful as hypoglycemic agents, and to a process for synthesis thereof The present invention also relates to the synthesis of 1-(aryloxy)propionoyl-2-arylsulfonyl hydrazines as new hypoglycemic agents which may be useful in the treatment of diabetes.
Introduction of more clinically effective hypoglycemic agents has been followed invariably by the rapid emergence of resistant antidiabetic drugs leading to increasing demand for new and potent hypoglycemic drugs. Acquisition of resistance has seriously reduced the therapeutic value of many known drugs including antidiabetics and has become a major stimulus to look for new moieties. Hence, the best approach is to look for new molecules structurally different from the existing drugs. The present invention relates to such an effort in developing title compounds as new hypoglycemic agents. These have not so far been investigated for the hypoglycemic activity and all compounds described are new molecules reported for the first time.
Reference may be made to Indian Drugs, 17, 315, 1980, wherein, authors have synthesized arylsulfonyl hydrazines as hypoglycemic agents. The drawbacks are that no substitutions were made to the hydrazine group which can improve the hypoglycemic activity. Incorporation of aryloxyalkyl substituents to organic moieties has been found to result in compounds which possess enhanced biological profile. Reference may also be made to Indian J. Chem:27B, 1057-1059, 1988, wherein authors have introduced substitutions by condensation of 4-chlorophenoxyacetic and isobutyric acid hydrazides with arylsulfonyl chlorides.
The main object of the present invention is to provide 1-(aryloxy)propionoyl-2-arylsulfonyl hydrazines which obviates the drawbacks as detailed above.
Another object of the present invention is to provide a process for the synthesis of 1-(aryloxy)propionoyl-2-arylsulfonyl hydrazines as potential hypoglycemic agents.
Still another object of the present invention is to unravel new hypoglycemic molecules structurally different from the known drugs such as Glibenclamide, Tolbutamide, Chloropropamide, Phenformin, Metformin, etc.
In the present invention, aryloxypropionic acid hydrazides were reacted with arylsulfonyl chlorides to obtain the title compounds as hypoglycemic agents for the first time.
Accordingly the present invention relates to 1-(aryloxy)propionoyl-2-arylsulfonyl hydrazine of the formula 
wherein R is selected from 4-Cl, 3-CH3-4-Cl and 2,4-Cl2, R1 is selected from H, Cl, and CH3.
In another embodiment of the invention, the 1-(aryloxy)propionoyl-2-arylsulfonyl hydrazine are selected from the following 
1-(aryloxy)propionoyl-2-arylsulfonyl hydrazine of the formula 
1-(aryloxy)propionoyl-2-arylsulfonyl hydrazine of the formula 
1-(aryloxy)propionoyl-2-arylsulfonyl hydrazine of the formula 
1-(aryloxy)propionoyl-2-arylsulfonyl hydrazine of the formula 
1-(aryloxy)propionoyl-2-arylsulfonyl hydrazine of the formula 
1-(aryloxy)propionoyl-2-arylsulfonyl hydrazine of the formula 
1-(aryloxy)propionoyl-2-arylsulfonyl hydrazine of the formula 
1-(aryloxy)propionoyl-2-arylsulfonyl hydrazine of the formula 
The present invention also provides a process for the synthesis of 1-(aryloxy)propionoyl-2-arylsulfonyl hydrazines useful as new oral hypoglycemic agents, which comprises reacting an aryloxypropionic acid hydrazide with an arylsulfonyl chloride.
In an embodiment of the present invention, aryloxy is selected from the group consisting of 4-chlorophenoxy, 3-methyl-4-chlorophenoxy and 2,4-dichlorophenoxy groups.
In another embodiment of the present invention, aryl is selected from the group consisting of phenyl, 4-chlorophenyl and 4-tolyl.